Optically Active H-Phosphinates and Their Stereospecific Transformations into Optically Active P-Stereogenic Organophosphoryl Compounds

Abstract

In this account, we summarize our recent work on the preparation of optically active H-phosphinates and their stereospecific transformations, including regio- and stereospecific additions, nucleophilic substitutions with organolithiums and Grignard reagents, halogenation with copper(II) chloride, and dehydrogenative couplings with heteroatom–hydrogen bonds. These reactions provide efficient ways for the synthesis of valuable, optically active, P-stereogenic, organophosphorus compounds from relatively easily prepared, enantiomerically pure, menthyl hydrogen phosphinates. The applications of optically active H-phosphinates in catalytic asymmetric hydrogenations are also discussed.

1 Optically Pure Menthyl Hydrogen Phosphinates: Easily Accessible P-Stereogenic Starting Materials

2 Optically Pure Menthyl Hydrogen Phosphinates as Starting Materials for the Synthesis of P-Chiral Compounds

2.1 Stereospecific Additions

2.1.1 Additions to Alkynes

2.1.2 Addition to Alkenes

2.1.3 Addition to p-Quinones

2.1.4 Additions to Ketones or Aldehydes

2.2 Stereospecific Nucleophilic Substitution by Organolithiums or Grignard Reagents

2.3 Stereospecific Halogenation with Copper(II) Chloride

2.4 Stereospecific Cross-Dehydrogenative Coupling with Nucleo­philes (Amines, Alcohols, Thiols, etc.)

2.5 Stereospecific Cross-Coupling with C–X Bonds

3 Asymmetric Catalytic Hydrogenation Reactions with Optically Pure Menthyl Hydrogen Phosphinates as Ligands

4 Conclusion

Key words

H-phosphinates - P-stereogenic organophosphorus compounds - stereoselectivity - transition metals - catalysis - asymmetric hydrogenation - nucleophilic substitutions

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